History • Architecture • Food • Beer

Experience Winchester VA Like Never Before

Discover Winchester one step, sip, bite at a time!

Explore the city’s unique and thriving food scene on our downtown Winchester walking mall food tours. Your experienced guide will introduce you to great local dishes and drinks while sharing stories about Winchester’s rich history and architecture.

Self Guided Historic Food Tour

Explore Winchester in this one of a kind historic food tour where you’ll learn about the founding events of Winchester, local architecture, and visit 5-6 restaurants. 

Fri, Sat, Sun
$25 per group

    positive review  We did the Taste of Winchester food and history tour today for my husband, Mike Gooden's birthday. It was very informative and enjoyable! Our hosts, Misty and Anthony, knew all of the restaurant owners and provided a wonderful way for us to try the different ethnic and American options right there on the pedestrian walkway...places we wouldn't have really noticed otherwise. We highly recommend the tour, especially if you are looking to expand the list of restaurants you frequent!

    Margy Weidenbruch Nolan Avatar Margy Weidenbruch Nolan
    January 12, 2020

    positive review  We had such a good time touring with Anthony and Misty on a rainy Sunday afternoon doing the History & Hops tour! We stopped at four places, and learned about the breweries, the beer, and a bit of Winchester history as well. They had a good relationship with each of the establishments and really catered to us in every way - from recommending beers to our palettes, taking our orders, and cleaning up afterwards, it was really above and beyond what you would expect from your tour guides. They are great conversationalists who will feel more like fast friends by the time your tour has ended. We will definitely try the Food tour that they offer the next time we are in Winchester for the holidays!

    Emmy Gottschalk Avatar Emmy Gottschalk
    December 30, 2019

    positive review  We had a great time on this food/history tour! Misty and Tony make a great team together. As I have not grown up in America the history information was so interesting for me to learn. Starting the tour at the Hideaway Cafe was great . Excellent sandwiches and good coffee to start . The different restaurants were amazing. I recommend this tour so much .

    Torsten Kiesewalter Avatar Torsten Kiesewalter
    September 15, 2018